Precise 1H- and 13C-NMR reassignment of dehydrocrebanine by 10-mg INADEQUATE and in silico analysis: With an alert for its toxicity

Chotika Phupong, Masahiko Suenaga, Phuangthip Bhoopong, Warangkana Chunglok, Gunlanan Jaritngam, Milandip Karak, Keiichi Yoshida, Worrapong Phupong, Kohei Torikai

Research output: Contribution to journalArticle

Abstract

During our continuous investigation on a Thai traditional medicinal plant, Stephania venosa Spreng, an alkaloid that seemed to be O-methyldehydrobulbocapnine (MDB) or dehydrocrebanine (DC), had been isolated. However, none of the previously reported 1H- and 13C-NMR data for MDB and DC matched our charts. Thus, we herein report the unambiguous determination of the alkaloid structure as DC via a successful INADEQUATE experiment using 10 mg of the unenriched natural specimen as well as an in silico estimation. Furthermore, our biological assay revealed that both the dichloromethane extract of S. venosa and the isolated DC show cytotoxicity to murine macrophage cells, which should be alerted to a folk doctor community that are using S. venosa to treat patients.

Original languageEnglish
Article number131310
JournalTetrahedron
Volume76
Issue number27
DOIs
Publication statusPublished - Jul 3 2020

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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